Fountains were particularly valued in fortified cities in the Middle Ages as were all things that aided survival during that period of war and bloodshed. The Branda fountain is certainly the oldest (late 12th Century); it is so old that even the days of the writer Bocaccio (1313-1375) it was considered to be ancient! The building is still there with its Guelph battlement.

The Piazza del Campo is a wonder of medieval construction in the heart of Siena. With the piazza's unique fishtail design constructed in rust-colored brick and white stone, the square is a result of excellent city planning. The square was built at the point where the original three towns that made up the city of Siena met and every building built around the square had to meet city guidelines so there was a sense of harmony. The brick laid square is divided into nine sections that represent each of the city's 'governo dei nove' or ruling governors. From a height, the sections look like the folds of a cloak believed to represent Mother Mary's cloak, Siena's patron saint. Today, the square hosts the popular bi-annual Palio or horse race that draws in visitors by the thousands waiting to see the majestic spectacle of thundering hooves.

A trip to Siena would be incomplete without visiting the Fonte Gaia. Standing over one of the most iconic squares in the city this imposing yet beautiful fountain was built in honor of the bride of God, Virgin Mary. Erected in 1342, a rectangular basin that was entirely made of marble was added to the original structure in 1419 by the highly acclaimed Early Renaissance sculptor, Jacopo della Quercia. The fountain is flanked by a set of thick marble panels which were installed to preserve some of the structure's intricate inscriptions and hand carvings.

Once one of the tallest secular towers in medieval Italy, the Torre del Mangia looms over the Piazza del Campo with its clock face, brick shaft, and stone and marble loggia. The tower was named after its first bell-ringer, nicknamed Mangiaguadagni, or ‘profit-eater,’ who was known to spend his earnings in local taverns. It is said that the part of the tower built in brick was a gesture toward the Italian commoner, while its height, which is the same as the city’s cathedral, was meant to signal that the adjacent town hall had power equal to the church. A climb to the top is rewarded with lovely views of the campo and Tuscan countryside.

Duomo di Siena, Siena's Cathedral, as it is seen today, stands on a plot of land that has always been dedicated to religion. Archaeological research has shown that there was a shrine built here as early as the 3rd Century. The Church of Santa Maria was built on top of that and then the current Duomo, which began at the end of the 12th Century. It is based on a Latin cross design with three naves. The polychrome marble facade is quite extraordinary. The entrance to the Libreria Piccolomini can be found in the nave on the left. The area dedicated to religious functions is enclosed and must not be entered during Mass as a sign of respect. Photographs are not allowed inside and all mobile phones should be turned off whether services are being held or not.

The library is located inside the Duomo and is worthy of a visit. It was founded in 1495 by Pope Pius III to hold the collection of his uncle Enea Silvio Piccolomini (Pope Pius II). The marble façade was designed by Marrina (1497) while all the perfectly preserved pictorial work was by Pinturicchio at the start of the 16th Century. The frescoes show episodes of the life of Pius II except for one on the entrance which illustrates the coronation of Pius III. There are superb choir books illuminated by Liberale da Verona, Girolamo da Verona, Sano di Pietro and others from 1469-75 which belong to the Duomo and the Spedale Santa Maria della Scala.

This is the third great building in the artistic and cultural triangle of Siena. It has been in use since the end of the 11th Century to aid the sick and the pilgrims that trod the Via Francigena from Canterbury to Rome, these pilgrims were referred to as "Romei". The various sections of the building really should be visited and the frescoes in the Pellegrino admired. Today, the building is open for visits and also houses museums and shops.

This street in Siena is best known for being an ideal location for passeggiata, a slow evening stroll common among locals. Upscale stores and shops line the road and draw many tourists for relaxing evenings of window shopping. Things are centered around the large retail anchor, Upim. Keep an eye out also for some great pastries, like the panforte at Nannini. This street is located near the Piazza del Campo.

The Basilica of San Domenico, also known as Basilica Cateriniana, is named after the catholic mystic and theologian Saint Catherine of Siena, whose family home is located nearby. The church contains several of the saint’s relics and her codex. Built by Dominicans on the hills of the Camporegio in the early 13th century, the church was expanded in the Gothic style two centuries later and is one of the most popular among tourists in Siena. Pilgrims are drawn to pray in front of the relics of Saint Catherine, who is one of the two patron saints of Italy along with Saint Francis of Assisi.